How One Woman Gamed The Online Dating System

Amy Webb learned how to crack the online dating code to meet her match.

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TallFriends.com, MilitaryFriends.com and Geek 2 Geek are all examples of niche dating sites.

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Amy Webb turned to online dating as a last resort—because she was 30 and newly single and so over playing the field. She cast a wide net, abandoning her picky tendencies in fear of overlooking the perfect man.

That's how she landed in a fancy Philadelphia restaurant with Jim, a foodie who liked to talk about cooking. He also liked ordering; in this case, an expensive bottle of wine, three appetizers, lamb chops, and Chilean sea bass. That same enthusiasm didn't extend to the $200 bill. Jim didn't even offer to split it, and the meal ended up costing Webb a chunk of her next month's rent.

"We were walking out, and I just wanted to get back to my car so I didn't have to deal with this guy anymore," says Webb, author of the new book Data, A Love Story. "He asked me if I smoked, and all of a sudden he pulled out this huge blunt and lit it up right there, in front of everybody. I really thought I had been roped into some kind of practical joke. But it wasn't a joke, it was real life."

That's around the time Webb realized her online dating profiles were attracting the wrong kind of men. Her dates were "horrifically bad—comically bad," she recalls. After one particularly disastrous night out, she decided to change her approach by drawing on her background in data analysis. Spoiler alert: Webb's memoir has a happy ending; she ultimately met her husband on JDate, a Jewish dating site. But as she explains in Data, A Love Story, gaming the online dating system to meet her match began with a list.

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Webb wrote down the 72 different attributes she would demand in a man, from the seemingly silly to the serious. There were the obvious standards, like smart and fun. But she also wanted someone with body hair (just not too much) who liked musicals and classic films, wasn't in debt, had an actual career, appreciated spreadsheets, and was willing to listen to George Michael. And then she realized: "I hadn't even stopped to think about my competitive set," Webb says. "I'd gotten this far and I suddenly thought, who am I up against?"

The solution: She outlined 10 male archetypes and created profiles for each of them on JDate, then spent a month perusing the site. She cataloged how women behaved and presented themselves online, scraping data from their profiles—like the language they used and number of hours they waited before responding to a note. "When I saw what was there, I was mortified and humiliated," Webb says. "I knew how bad my profile was, and what damage I'd done to myself because of what I posted. I had essentially copied and pasted my resumé."

If a dating profile is going to catch male attention, it needs to be short, casual, and fun, Webb learned. And that's just one of many lessons. The patterns she observed can help anyone trying to stand out in the virtual dating pool:

Popular profiles use aspirational language. Rather than opening your profile with a description of your job or accomplishments, use positive, optimistic language to describe your hopes, dreams, interests, and hobbies. And don't write too much: There's a direct correlation between profile length and the likability of the person it represents, Webb found. In the opening section, aim for fewer than 100 words, or about three sentences.

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Popular women make the first move. Grow up hearing that men don't want to be pursued, and you should wait for him to come to you? Webb did. But her experiment proved that the popular women in the online world made the first move when they wanted to. "It's totally OK, as long as you're not being ridiculous about it," she says. "In the real world, you wouldn't make a sexual joke the first time you meet someone, but for some reason a lot of people do that online. Try not to abandon your common sense and awareness of social cues."

Women with curly hair have less luck. Webb's experiment suggests that men prefer women with healthy, long, straight hair. If you have curls, try straightening your locks, she says—if you're comfortable doing so, of course.